Sulphonyl amino (thio) carbonyl-1,2,4-triazolin (thi) one derivatives and the use thereof as herbicides

ABSTRACT

The invention relates to sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) ##STR1## in which Q 1  represents oxygen or sulphur, 
     Q 2  represents oxygen or sulphur, 
     R 1  represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl and arylalkyl, 
     R 2  represents hydrogen, hydroxyl, mercapto, amino, halogen or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, alkenylamino, alkinylamino, dialkylamino, alkanoylamino, aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino and arylalkylamino, or 
     R 1  and R 2  together represent optionally branched alkanediyl, and 
     R 3  represents respectively optionally substituted aryl, arylalkyl or heteroaryl, 
     with the proviso that either Q 1  or Q 2  represents sulphur or both represent sulphur, and to salts of the compounds of the formula (I), furthermore to a plurality of processes for preparing the novel compounds of the formula (I) and the salts thereof and to the use of these compounds as herbicides.

The invention relates to sulphonylamino(thio)carbonyl-triazolin(ethi)ones containing at least one thiocarbonyl group [--C(═S)--], to a plurality of processes for their preparation, and to their use as herbicides.

It is known that certain sulphonylaminocarbonyltriazolinones have herbicidal properties (cf. EP-A 341489, EP-A 422469, EP-A 425948, EP-A 431291). However, sulphonylamino(thio)carbonyl-triazolin(ethi)ones having at least one thiocarbonyl group have hitherto not been disclosed.

This invention, then, provides the novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) ##STR2## in which

Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl and arylalkyl,

R² represents hydrogen, hydroxyl, mercapto, amino, halogen or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, alkenylamino, alkinylamino, dialkylamino, alkanoylamino, aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino and arylalkylamino, or

R¹ and R² together represent optionally branched alkanediyl, and

R³ represents respectively optionally substituted aryl, arylalkyl or heteroaryl,

with the proviso that either Q¹ or Q² represents sulphur or both represent sulphur, and salts of the compounds of the formula (I).

The novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) are obtained when

(a) triazolin(ethi)ones of the general formula (II) ##STR3## in which

Q¹, R¹ and R² are each as described above, are reacted with sulphonyl iso(thio)cyanates of the general formula (III)

    R.sup.3 --SO.sub.2 --N═C═Q.sup.2                   (III)

in which

Q² and R³ are each as described above,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or

(b) triazolin(ethi)one derivatives of the general formula (IV) ##STR4## in which

Q¹, Q², R¹ and R² are each as described above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reacted with sulphonamides of the general formula (V)

    R.sup.3 --SO.sub.2 --NH.sub.2                              (V)

in which

R³ is as described above,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or

(c) triazolin(ethi)ones of the general formula (II) ##STR5## in which

Q¹, R¹ and R² are each as described above, are reacted with sulphonamide derivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CQ.sup.2 --Z                      (VI)

in which

Q² and R³ are each as described above and

Z represents halogen, alkoxy, aryloxy or arylalkoxy,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or

(d) triazolin(ethi)ones of the general formula (II) ##STR6## in which

Q¹, R¹ and R² are each as described above, are reacted with sulphonyl halides of the general formula (VII)

    R.sup.3 --SO.sub.2 --X                                     (VII)

in which

R¹ is as described above and

X represents halogen,

and metal (thio)cyanates of the general formula (VIII)

    MQ.sup.2 CN                                                (VIII)

in which

Q² is as described above and

M represents an alkali metal or an alkaline earth metal equivalent,

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are, if desired, converted into salts by customary methods.

The novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) have strong herbicidal action.

The invention preferably relates to compounds of the formula (I) in which

Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents hydrogen, hydroxyl or amino, or represents C₂ -C₁₀ -alkylideneamino or represents optionally fluorine-, chlorine-, bromine-, cyano-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆ -alkyl, or represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C₂ -C₆ -alkenyl or C₂ -C₆ -alkinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, C₁ -C₄ -alkoxy- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆ -alkoxy, C₁ -C₆ -alkylamino or C₁ -C₆ -alkanoylamino, or represents C₃ -C₆ -alkenyloxy, or represents di-(C₁ -C₄ -alkyl)-amino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkylamino or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁ -C₄ -alkyl-, trifluoromethyl- and/or C₁ -C₄ -alkoxy-substituted phenyl or phenyl-C₁ -C₄ -alkyl,

R² represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine, bromine or iodine, or represents optionally fluorine-, chlorine-, bromine-, cyano-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆ -alkyl, or represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C₂ -C₆ -alkenyl or C₂ -C₆ -alkinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, C₁ -C₄ -alkoxy- or C₁ -C₄ -alkoxy-carbonyl-substituted C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino or C₁ -C₆ -alkanoylamino, or represents C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkinyloxy, C₃ -C₆ -alkenylthio, C₃ -C₆ -alkinylthio, C₃ -C₆ -alkenylamino or C₃ -C₆ -alkinylamino, or represents di-(C₁ -C₄ -alkyl)-amino, or represents respectively optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C₁ -C₄ -alkyl-substituted C₃ -C₆ -cycloalkyl, C₅ -C₆ -cycloalkenyl, C₃ -C₆ -cycloalkyloxy, C₃ -C₆ -cycloalkylthio, C₃ -C₆ -cycloalkylamino, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkoxy, C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkylthio or C₃ -C₆ -cycloalkyl-C₁ -C₄ -alkylamino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C₁ -C₄ -alkyl-, trifluoromethyl- and/or C₁ -C₄ -alkoxy-substituted phenyl, phenyl-C₁ -C₄ -alkyl, phenoxy, phenyl-C₁ -C₄ -alkoxy, phenylthio, phenyl-C₁ -C₄ -alkylthio, phenylamino or phenyl-C₁ -C₄ -alkylamino, or

R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and

R³ represents the grouping ##STR7## in which

R⁴ and R⁵ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl, di-(C₁ -C₄ -alkyl)-amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxy-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆ -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₂ -C₆ -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆ -alkinylthio, or represent the radical --S(O)_(p) --R⁶ in which

p represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino or phenyl, or represent the radical --NHOR⁷ in which

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C₃ -C₆ -alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl or phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or represents benzhydryl or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxy-carbonyl),

R⁴ and R⁵ further represent phenyl or phenoxy, or represent C₁ -C₄ -alkyl-carbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄ -alkylamino-carbonyl-amino or di-(C₁ -C₄ -alkyl)-amino-carbonylamino, or represent the radical --CO--R⁸ in which

R⁸ represents hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (each of which is optionally substituted by fluorine and/or chlorine),

R⁴ and/or R⁵ further represent trimethylsilyl, thiazolinyl, C₁ -C₄ -alkyl-sulphonyloxy or di-(C₁ -C₄ -alkyl)-aminosulphonylamino, or represent the radical --CH═N--R⁹ in which

R⁹ represents optionally fluorine-, chlorine-, cyano-, carboxyl-, C₁ -C₄ -alkoxy-, C₁ -C₄ -alkylthio-, C₁ -C₄ -alkylsulphinyl- or C₁ -C₄ -alkylsulphonyl-substituted C₁ -C₆ -alkyl, or represents optionally fluorine- or chlorine-substituted benzyl, or represents optionally fluorine- or chlorine-substituted C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, or represents optionally fluorine-, chlorine-, bromine-, C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, or represents optionally fluorine- and/or chlorine-substituted C₁ -C₆ -alkoxy, C₃ -C₆ -alkenyloxy, C₃ -C₆ -alkinyloxy or benzyloxy, or represents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonyl-amino, C₁ -C₄ -alkoxy-carbonylamino or C₁ -C₄ -alkyl-sulphonylamino, or represents optionally fluorine-, chlorine-, bromine- or methyl-substituted phenylsulphonylamino, furthermore,

R³ represents the radical ##STR8## in which

R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl or di-(C₁ -C₄ -alkyl)-aminosulphonyl; furthermore,

R³ represents the radical ##STR9## in which

R¹³ and R¹⁴ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine); furthermore,

R³ represents the radical ##STR10## in which

R¹⁵ and R¹⁶ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl or mono-(C₁ -C₄ -alkyl)-aminosulphonyl, or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl or C₁ -C₄ -alkoxy-carbonyl or dimethyl-aminocarbonyl; furthermore,

R³ represents the radical ##STR11## in which

R¹⁷ and R¹⁸ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or bromine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl; furthermore,

R³ represents the radical ##STR12## in which

R¹⁹ and R²⁰ are identical or different and each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl, and

A represents oxygen, sulphur or the grouping N--Z¹ in which

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C₃ -C₆ -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl; furthermore,

R³ represents the radical ##STR13## in which

R²¹ and R²² are identical or different and each represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the grouping N--R²³ in which

R²³ represents hydrogen or C₁ -C₄ -alkyl; furthermore,

R³ represents the radical ##STR14## in which

R²⁴ represents hydrogen, C₁ -C₄ -alkyl, benzyl, pyridyl, quinolinyl or phenyl, R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C₁ -C₄ -alkoxy-carbonyl, and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl, and furthermore,

R³ represents one of the groupings listed below ##STR15## with the proviso that either Q¹ or Q² represents sulphur or that both represent sulphur.

The invention further preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, tetra-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-sulphonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which Q¹, Q², R¹, R² and R³ are preferably as defined above.

The invention in particular relates to compounds of the formula (I) in which

Q¹ represents oxygen or sulphur,

Q² represents oxygen or sulphur,

R¹ represents hydrogen, hydroxyl or amino, or represents C₃ -C₈ -alkylideneamino or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexyl-amino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl,

R² represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine or bromine, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or

R¹ and R² together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and

R³ represents the radical ##STR16## in which

R⁴ represents fluorine, chlorine or bromine, or represents respectively optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, or represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl or phenoxy, or represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and

R⁵ represents hydrogen, methyl, ethyl, fluorine, chlorine or bromine; furthermore,

R³ represents the radical ##STR17## in which

R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and

R¹² represents hydrogen; furthermore,

R³ represents the radical ##STR18## in which

R represents methyl, ethyl, n- or i-propyl, or

R³ represents the radical ##STR19## in which

R²⁴ represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl,

R²⁵ represents hydrogen, fluorine, chlorine or bromine,

R²⁶ represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl,

with the proviso that either Q¹ or Q² represents sulphur or that both represent sulphur.

The radical definitions listed above, whether general or in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, thus including combinations between the preferred ranges indicated.

In the definitions of the radicals, hydrocarbon radicals such as alkyl, alkenyl or alkinyl, are, even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino, even if this is not explicitly stated, straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Examples of the meaning of the radicals R¹, R² and R³ in the compounds of the formula (I) according to the invention are listed in the groups below.

Group 1 ##STR20##

R¹ has, for example, the meanings listed below: amino, n- or i-propylideneamino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dichloropropyl, dibromopropyl, methoxypropyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, propenyloxy, dimethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl-cyclopropyl or cyclopropylmethyl.

R² has, for example, the meanings listed below: hydrogen, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, fluoromethylthio, chloromethylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, trifluoroethylthio, trifluoropropylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propenylamino, butenylamino, propinylamino, butinylamino, dimethylamino, diethylamino, N-methyl-ethylamino, N-methyl-propylamino, N-ethyl-propylamino, cyclopropyl, cyclopropyloxy, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethylthio, phenyl, phenoxy, phenylthio, phenylamino, phenylmethyl, phenylmethoxy, phenylmethylthio or phenylmethylamino.

Additionally, R¹ and R² together have, for example, the following meanings: propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl and undecane-1,11-diyl.

R³ has, for example, the meanings listed below: 2-fluoro-phenyl, 2-chloro-phenyl, 2-bromo-phenyl, 2,6-difluoro-phenyl, 2,6-dichloro-phenyl, 2-methyl-phenyl, 2-chloro-6-methyl-phenyl, 2-trifluoromethyl-phenyl, 2-(2-fluoro-ethyl)-phenyl, 2-(2-chloro-ethyl)-phenyl, 2-(3-fluoro-propyl)-phenyl, 2-(3-chloro-propyl)-phenyl, 2-(3,3,3-trifluoro-propyl)-phenyl, 2-(3,3,3-trifluoro-1-propenyl)-phenyl, 2-methoxy-phenyl, 2-ethoxy-phenyl, 2-difluoromethoxy-phenyl, 2-trifluoromethoxy-phenyl, 2-(2-fluoro-ethoxy)-phenyl, 2-(2-chloro-ethoxy)-phenyl, 2-(2-methoxy-ethoxy)-phenyl, 2-methylthio-phenyl, 2-ethylthio-phenyl, 2-methylsulphinyl-phenyl, 2-ethylsulphinyl-phenyl, 2-methylsulphonyl-phenyl, 2-ethylsulphonyl-phenyl, 2-dimethylaminosulphonyl -phenyl, 2-phenyl-phenyl, 2-methoxycarbonyl-phenyl, 2-ethoxycarbonyl-phenyl, 2-chloro-phenylmethyl, 2,6-dichloro-phenylmethyl, 2-difluoromethoxy-phenylmethyl, 2-trifluoromethoxy-phenylmethyl, 2-methoxycarbonyl-phenylmethyl, 2-ethoxycarbonyl-phenylmethyl, 2-methoxycarbonyl-3-thienyl,2-ethoxycarbonyl-3-thienyl, 4-methoxycarbonyl-1-methyl-5-pyrazolyl, 4-ethoxycarbonyl-1-methyl-5-pyrazolyl, 3-chloro-4-methoxycarbonyl-1-methyl-5-pyrazolyl, 3-chloro-4-ethoxycarbonyl- 1 -methyl-5-pyrazolyl, 3-methoxycarbonyl-2-pyridyl, 3-ethoxycarbonyl-2-pyridyl, 3-dimethylaminocarbonyl-2-pyridyl, 3-methylsulphonyl-2-pyridyl or 3-ethylsulphonyl-2-pyridyl.

Group 2 ##STR21##

R¹, R² and R³ have, for example, the meanings listed above in group 1 under formula (IA).

Group 3 ##STR22##

R¹, R² and R³ have, for example, the meanings listed above in group 1 under formula (IA).

Using, for example, 2,6-difluoro-phenyl isocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazole-3-thione as starting materials, the course of reaction in the process (a) according to the invention can be illustrated by the following equation: ##STR23##

Using, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation: ##STR24##

Using, for example, N-methoxythiocarbonyl-2-methoxy-benzenesulphonamide and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following equation: ##STR25##

Using, for example, 4-ethyl-5-ethylthio-2,4-dihydro-3H-1,2,4-triazole-3-thione and 2-bromo-benzenesulphonyl chloride and potassium thiocyanate as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation: ##STR26##

A general definition of the triazolin(ethi)ones to be used as starting materials in the processes (a), (c) and (d) according to the invention for preparing compounds of the formula (I) is given by the formula (II).

In the formula (II), Q¹, R¹ and R² each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for Q¹, R² and R².

The triazolin(ethi)ones of the general formula (II) are known and/or can be prepared by methods known per se (cf. Arch. Pharm. 301 (1968), 827; loc. cit. 307 (1974), 889; Bull. Soc. Chim. France 1962, 1365; loc. cit. 1975, 1191; Chem. Ber. 90 (1957), 909-921; loc. cit. 98 (1965), 3025-3099; loc. cit. 102 (1969), 755; J. Heterocycl. Chem. 15 (1978), 237-240; J. Indian Chem. Soc. 6 (1929), 565; Liebigs Ann. Chem. 637 (1960), 135; Monatshefte Chemie 123 (1992), 257; Tetrahedron 32 (1976), 2347-2352; Helv. Chim. Acta 63 (1980), 841-859; J. Chem. Soc. C 1967, 746-751; loc. cit. 1970, 26-34; J. Chem. Soc. Perkin I 1973, 2644; Fen Fak. Derg., Seri A (Ege Univ.) 7 (1984), 1-6--quoted in Chem. Abstracts 101:90846m; EP-A 283876; EP-A 294666; EP-A 298371; EP-A 301946; EP-A 305844; EP-A 341489; EP-A 362633; EP-A 370293; EP-A 391187; EP-A 398096; EP-A 398097; EP-A 399294; EP-A 415196; EP-A 422469; EP-A 425948; EP-A 431291; EP-A 477646; EP-A 502307; EP-A 503437; EP-A 505819; EP-A 511569; EP-A 513621; DE-A 2336827; DE-A 3839206; DE-A 3916208; DE-A 3916930; DD-P 64970; WO-A 93/04050; Preparation Examples).

A general definition of the sulphonyl iso(thio)cyanates also to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I) is given by the formula (III).

In the formula (III), Q² and R³ each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention as being preferable or particularly preferable for Q² and R³.

The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,371,391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).

A general definition of the triazolin(ethi)one derivatives to be used as starting materials in the process (b). according to the invention for preparing compounds of the general formula (I) is given by the formula (IV). In the formula (IV), Q¹, Q², R¹ and R² each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (1), as being preferable or particularly preferable for Q¹, Q², R¹ and R² ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogeno- or nitro-phenoxy, and in particular represents methoxy, phenoxy or 4-nitro-phenoxy.

The starting materials of the formula (IV) have not been disclosed in the literature; as novel substances, they are also part of the subject matter of the present application. The novel compounds of the general formula (IV) are obtained when triazolin(ethi)ones of the general formula (II) ##STR27## in which

Q¹, R¹ and R² are each as defined above,

are reacted with (thio)carbonic acid derivatives of the general formula (IX)

    Z--CQ.sup.2 --Z.sup.1                                      (IX)

in which

Z and Q² are each as defined above and

Z¹ represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor, such as, for example, sodium hydroxide or potassium hydroxide, sodium t-butoxide or potassium t-butoxide, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, tetrahydrofuran or dimethoxyethane and/or water, at temperatures between 0° C. and 100° C.

A general definition of the sulphonamides also to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (V). In the formula (V), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R³.

The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,371,391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).

A general definition of the sulphonamide derivatives to be used as starting materials in the process (c) according to the invention for preparing compounds of the general formula (I) is given by the formula (VI). In the formula (VI), Q² and R³ each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for Q² and R³ ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, and in particular represents methoxy or phenoxy.

The starting materials of the formula (VI) are known and/or can be prepared by methods known per se.

A general definition of the sulphonyl halides to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I) is given by the formula (VII). In the formula (VII), R³ preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R³ ; X preferably represents fluorine, chlorine or bromine, and in particular represents chlorine.

The starting materials of the formula (VII) are known and/or can be prepared by methods known per se.

The processes (a), (b), (c) and (d) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate; nitriles, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preference is given to alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alkoxides, such as sodium carbonate and potassium carbonate, sodium tert-butoxide and potassium tert-butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).

The reaction temperatures in the processes (a), (b), (c) and (d) according to the invention can be varied within a relatively wide range. The reactions are in general carried out at temperatures of between -20° C. and +150° C., preferably at temperatures between 0° C. and +100° C.

The processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

For carrying out processes (a), (b), (c) and (d) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Work-up in the case of the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methds (cf. the Preparation Examples).

Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then--if desired after prolonged stirring--be isolated by concentration or filtration with suction.

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindemia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial crops, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention are preferably suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre-emergence and post-emergence.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, ready-to-use formulations or tank mixes being possible.

Possible components for the mixtures are known herbicides, for example anilides, such as diflufenican and propanil; arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, such as chlorotoluron, diuron, fluometuron, isproturon, linuron and methabenzthiazuron; hydroxylamines, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as bromoxynil, dichlobenil and ioxynil; oxyacetamides, such as mefenacet; sulphonyl-ureas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, such as hexazinone, metamitron and metribuzin; others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, defenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 10 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR28## (by process (a))

A mixture of 3.0 g (20.7 mmol) of 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 4.8 g (20.7 mmol) of 3-chloro-phenylsulphonyl isothiocyanate, 0.3 g of triethylamine and 60 ml of acetonitrile is heated under reflux for 12 hours and then concentrated under water pump vacuum. The residue is stirred with diethyl ether and the crystalline product is isolated by filtration under suction.

2.1 g (27% of theory) of 2-(3-chloro-phenylsulphonyl-aminothiocarbonyl)-4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 141° C. are obtained.

Example 2 ##STR29## (by process (b))

A mixture of 3.2 g (12 mmol) of 5-methoxy-4-methyl-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.9 g (12 mmol) of 2-trifluoromethoxy-benzene-sulphonamide, 1.9 g (12.5 mmol) of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 30 ml of dioxane is stirred at 20° C. for 12 hours. The mixture is then diluted with methylene chloride and water and the pH is adjusted to 3 using 2N hydrochloric acid. The organic phase is then separated off, dried with sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is crystallized by digestion with diethyl ether and the product is isolated by filtration under suction.

3.1 g (63% of theory) of 5-methoxy-4-methyl-2-(2-trifluoromethoxy-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 139° C. are obtained.

Example 3 ##STR30## (by process (b))

At 20° C., 28.1 g (0.125 mol) of 2-trifluoromethyl-benzenesulphonamide and a solution of 19 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) in 50 ml of acetonitrile are added in succession to a solution of 28.1 g (0.10 mol) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 300 ml of acetonitrile. The reaction mixture is stirred at 20° C. until a clear solution is obtained. The solution is then concentrated under water pump vacuum and the residue is admixed with water and methylene chloride (300 ml each) and acidified with 2N hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted once more with 100 ml of methylene chloride and the combined organic phases are dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is crystallized from isopropanol.

29.6 g (72% of theory) of 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 154° C. are obtained.

By the methods of Examples 1, 2 and 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below. ##STR31##

                                      TABLE 1                                      __________________________________________________________________________     Examples of compounds of the formula (I)                                       Ex.                               Melting                                      No.                                                                               Q.sup.1                                                                          Q.sup.2                                                                          R.sup.1 R.sup.2                                                                              R.sup.3      point (° C.)                          __________________________________________________________________________      4 O S CH.sub.3                                                                               OC.sub.3 H.sub.7                                                                     1             94                                           5 S O CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      2 #STR32##   126                                           6 O S CH.sub.3                                                                               SCH.sub.3                                                                            3 #STR33##   142                                           7 O S CH.sub.3                                                                               SCH.sub.3                                                                            4 #STR34##   186                                           8 O S CH.sub.3                                                                               SCH.sub.3                                                                            5 #STR35##   174                                           9 O S CH.sub.3                                                                               SCH.sub.3                                                                            6 #STR36##   196                                           10                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            7 #STR37##   194                                           11                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            8 #STR38##   143                                           12                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            9 #STR39##   159                                           13                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            0 #STR40##   156                                           14                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            1 #STR41##   139                                           15                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            1 #STR42##   151                                           16                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            7 #STR43##   125                                           17                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            2 #STR44##   164                                           18                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            3 #STR45##   149                                           19                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            4 #STR46##   156                                           20                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            5 #STR47##   157                                           21                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            6 #STR48##   171                                           22                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            7 #STR49##   134                                           23                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            8 #STR50##   139                                           24                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            9 #STR51##   134                                           25                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            0 #STR52##   140                                           26                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            1 #STR53##   125                                           27                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      2 #STR54##   126                                           28                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     2 #STR55##   152                                           29                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      0 #STR56##   128                                           30                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      1 #STR57##   103                                           31                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      7 #STR58##    92                                           32                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      2 #STR59##   111                                           33                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      3 #STR60##   141                                           34                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     0 #STR61##   142                                           35                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     1 #STR62##   133                                           36                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     7 #STR63##   110                                           37                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     2 #STR64##   131                                           38                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     3 #STR65##   156                                           39                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     2 #STR66##   141                                           40                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     4 #STR67##   160                                           41                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     4 #STR68##   155                                           42                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     5 #STR69##   123                                           43                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     6 #STR70##   127                                           44                                                                               O S CH.sub.3                                                                               OCH.sub.3                                                                            2 #STR71##   155                                           45                                                                               O S --(CH.sub.2).sub.5 --                                                                        1 #STR72##   128                                           46                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     1 #STR73##   147                                           47                                                                               O S OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                     2 #STR74##   114                                           48                                                                               O S OC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.5                                                                     1 #STR75##   113                                           49                                                                               O S N(CH.sub.3).sub.2                                                                      C.sub.3 H.sub.7 -n                                                                   2 #STR76##   113                                           50                                                                               O S N(CH.sub.3).sub.2                                                                      C.sub.3 H.sub.7 -n                                                                   1 #STR77##   114                                           51                                                                               O S                                                                                6 #STR78##                                                                             OC.sub.3 H.sub.7 -i                                                                  2 #STR79##    74                                           52                                                                               O S                                                                                6 #STR80##                                                                             OC.sub.3 H.sub.7 -i                                                                  1 #STR81##   119                                           53                                                                               O S                                                                                6 #STR82##                                                                             N(CH.sub.3).sub.2                                                                    2 #STR83##   131                                           54                                                                               O S                                                                                6 #STR84##                                                                             N(CH.sub.3).sub.2                                                                    1 #STR85##   132                                           55                                                                               O S                                                                                6 #STR86##                                                                             6 #STR87##                                                                           2 #STR88##   114                                           56                                                                               O S                                                                                6 #STR89##                                                                             6 #STR90##                                                                           1 #STR91##   124                                           57                                                                               O S                                                                                6 #STR92##                                                                             SC.sub.2 H.sub.5                                                                     2 #STR93##   123                                           58                                                                               O S                                                                                6 #STR94##                                                                             SC.sub.2 H.sub.5                                                                     1 #STR95##   125                                           59                                                                               O S OCH.sub.3                                                                              SCH.sub.3                                                                            2 #STR96##   110                                           60                                                                               O S OCH.sub.3                                                                              SCH.sub.3                                                                            1 #STR97##   127                                           61                                                                               O S OCH.sub.3                                                                              SC.sub.2 H.sub.5                                                                     2 #STR98##   121                                           62                                                                               O S OCH.sub.3                                                                              SC.sub.2 H.sub.5                                                                     1 #STR99##   122                                           63                                                                               O S CH.sub.3                                                                               CH.sub.3                                                                             2 #STR100##  119                                           64                                                                               O S CH.sub.3                                                                               CH.sub.3                                                                             1 #STR101##  122                                           65                                                                               O S CH.sub.3                                                                               CH.sub.3                                                                             1 #STR102##  113                                           66                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      1 #STR103##  118                                           67                                                                               O S CH.sub.3                                                                               C.sub.3 H.sub.7 -n                                                                   2 #STR104##  112                                           68                                                                               O S CH.sub.3                                                                               C.sub.3 H.sub.7 -n                                                                   1 #STR105##  112                                           69                                                                               O S CH.sub.3                                                                               C.sub.3 H.sub.7 -i                                                                   2 #STR106##  119                                           70                                                                               O S CH.sub.3                                                                               C.sub.3 H.sub.7 -i                                                                   1 #STR107##  101                                           71                                                                               O S CH.sub.3                                                                               C.sub.3 H.sub.7 -i                                                                   1 #STR108##  118                                           72                                                                               O S CH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                   2 #STR109##  124                                           73                                                                               O S CH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                   1 #STR110##  108                                           74                                                                               O S CH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                   1 #STR111##  106                                           75                                                                               O S CH.sub.3                                                                               SC.sub.2 H.sub.5                                                                     2 #STR112##  129                                           76                                                                               O S CH.sub.3                                                                               SC.sub.2 H.sub.5                                                                     1 #STR113##  131                                           77                                                                               O S CH.sub.3                                                                               SC.sub.2 H.sub.5                                                                     1 #STR114##  135                                           78                                                                               O S CH.sub.3                                                                               OCH.sub.3                                                                            1 #STR115##  131                                           79                                                                               O S C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                     2 #STR116##  128                                           80                                                                               O S C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.5                                                                     1 #STR117##   85                                           81                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -n                                                                  2 #STR118##  108                                           82                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -n                                                                  2 #STR119##  122                                           83                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -i                                                                  1 #STR120##  119                                           84                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -i                                                                  1 #STR121##  130                                           85                                                                               O S C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            2 #STR122##  123                                           86                                                                               O S C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            1 #STR123##  132                                           87                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      1 #STR124##  109                                           88                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      1 #STR125##  105                                           89                                                                               O S CH.sub.3                                                                               Br                                                                                   2 #STR126##  126                                           90                                                                               O S CH.sub.3                                                                               Br                                                                                   1 #STR127##  115                                           91                                                                               O S CH.sub.3                                                                               Br                                                                                   1 #STR128##  113                                           92                                                                               O S                                                                                6 #STR129##                                                                            Br                                                                                   2 #STR130##  113                                           93                                                                               O S                                                                                6 #STR131##                                                                            Br                                                                                   1 #STR132##  107                                           94                                                                               O S                                                                                6 #STR133##                                                                            Br                                                                                   1 #STR134##  103                                           95                                                                               O S                                                                                6 #STR135##                                                                            OC.sub.2 H.sub.5                                                                     2 #STR136##  117                                           96                                                                               O S                                                                                6 #STR137##                                                                            OC.sub.2 H.sub.5                                                                     1 #STR138##  105                                           97                                                                               O S                                                                                6 #STR139##                                                                            OC.sub.2 H.sub.5                                                                     1 #STR140##   90                                           98                                                                               O S                                                                                6 #STR141##                                                                            CH.sub.2 OCH.sub.3                                                                   2 #STR142##  106                                           99                                                                               O S                                                                                6 #STR143##                                                                            CH.sub.2 OCH.sub.3                                                                   1 #STR144##  119                                          100                                                                               O S                                                                                6 #STR145##                                                                            CH.sub.2 OCH.sub.3                                                                   1 #STR146##  110                                          101                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      7 #STR147##  119                                          102                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      5 #STR148##  126                                          103                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      6 #STR149##  122                                          104                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      6 #STR150##  127                                          105                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      8 #STR151##  129                                          106                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     7 #STR152##  137                                          107                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     6 #STR153##  127                                          108                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     8 #STR154##  151                                          109                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      8 #STR155##  141                                          110                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      7 #STR156##  143                                          111                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            9 #STR157##  130                                          112                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      4 #STR158##  128                                          113                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      0 #STR159##  115                                          114                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      3 #STR160##  108                                          115                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      8 #STR161##  129                                          116                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      9 #STR162##  128                                          117                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     4 #STR163##  130                                          118                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     0 #STR164##  135                                          119                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     3 #STR165##  145                                          120                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     8 #STR166##  128                                          121                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     9 #STR167##  121                                          122                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      1 #STR168##   92                                          123                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      0 #STR169##  115                                          124                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     1 #STR170##  147                                          125                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     0 #STR171##  132                                          126                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            1 #STR172##  138                                          127                                                                               O S                                                                                6 #STR173##                                                                            OC.sub.2 H.sub.5                                                                     0 #STR174##  137                                          128                                                                               O S                                                                                6 #STR175##                                                                            OC.sub.2 H.sub.5                                                                     2 #STR176##  105                                          129                                                                               O S                                                                                6 #STR177##                                                                            OC.sub.2 H.sub.5                                                                     3 #STR178##  122                                          130                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      2 #STR179##  102                                          131                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      3 #STR180##   97                                          132                                                                               O S                                                                                6 #STR181##                                                                            Br                                                                                   2 #STR182##  132                                          133                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      0 #STR183##                                               134                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      2 #STR184##  112                                          135                                                                               O S                                                                                6 #STR185##                                                                            Br                                                                                   4 #STR186##  118                                          136                                                                               O S CH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                   2 #STR187##  100                                          137                                                                               O S                                                                                6 #STR188##                                                                            Br                                                                                   3 #STR189##                                               138                                                                               O S CH.sub.3                                                                               CH.sub.2 OCH.sub.3                                                                   0 #STR190##                                               139                                                                               O S CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                   2 #STR191##   73                                          140                                                                               O S CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                   1 #STR192##  107                                          141                                                                               O S CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                   1 #STR193##  116                                          142                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -n                                                                  1 #STR194##                                               143                                                                               O S OCH.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                                                      1 #STR195##                                               144                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     9 #STR196##                                               145                                                                               O S C.sub.2 H.sub.5                                                                        OCH.sub.3                                                                            1 #STR197##  143                                          146                                                                               O S OCH.sub.3                                                                              C.sub.3 H.sub.7 -n                                                                   1 #STR198##   98                                          147                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            5 #STR199##   1 208 1 (Na salt)                           148                                                                               O S CH.sub.3                                                                               SCH.sub.3                                                                            2 #STR200##   1 237 1 (Na salt)                           149                                                                               O S CH.sub.3                                                                               OCH.sub.3                                                                            2 #STR201##   1 210 1 (Na salt)                           150                                                                               O S CH.sub.3                                                                               OCH.sub.3                                                                            1 #STR202##   1 216 1 (Na salt)                           151                                                                               O S CH.sub.3                                                                               OC.sub.2 H.sub.5                                                                     1 #STR203##   1 211 1 (Na salt)                           152                                                                               O S CH.sub.3                                                                               OC.sub.3 H.sub.7 -n                                                                  1 #STR204##   1 217 1 (Na salt)                           153                                                                               O S CH.sub.3                                                                               C.sub.2 H.sub.5                                                                      9 #STR205##   40                                          154                                                                               O S --CH.sub.2 CH═CH.sub.2                                                             OC.sub.2 H.sub.5                                                                     0 #STR206##  130                                          155                                                                               O S --CH.sub.2 CH═CH.sub.2                                                             OC.sub.2 H.sub.5                                                                     1 #STR207##   84                                          156                                                                               O S --CH.sub.2 CH═CH.sub.2                                                             OC.sub.2 H.sub.5                                                                     2 #STR208##   85                                          157                                                                               O S                                                                                6 #STR209##                                                                            OC.sub.2 H.sub.5                                                                     1 #STR210##   1 205 1 (Na salt)                           158                                                                               O S                                                                                6 #STR211##                                                                            Br                                                                                   1 #STR212##   1 212 1 (Na salt)                           159                                                                               O S                                                                                6 #STR213##                                                                            Br                                                                                   1 #STR214##   1 220 1 (Na salt)                           160                                                                               O S                                                                                6 #STR215##                                                                            Br                                                                                   2 #STR216##   1 150 1 (Na salt)                           161                                                                               O S CH.sub.3                                                                               --CH.sub.2 OCH.sub.3                                                                 1 #STR217##   1 205 1 (Na salt)                           162                                                                               O S CH.sub.3                                                                               --CH.sub.2 OCH.sub.3                                                                 2 #STR218##   1 165 1 (Na salt)                           163                                                                               O S                                                                                6 #STR219##                                                                            OC.sub.2 H.sub.5                                                                     5 #STR220##  128                                          164                                                                               O S OC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                      5 #STR221##  120                                          __________________________________________________________________________

Starting materials of the formula (II):

Example (II-1) ##STR222##

A mixture of 4.0 g (20 mmol) of the potassium salt of 4-ethoxy-5-mercapto-2,4-dihydro-3H-1,2,4-triazol-3-one, 4.3 g (30 mmol) of methyl iodide and 50 ml of methanol is stirred at 20° C. for 16 hours and then concentrated. The residue is extracted with methylene chloride/water and the organic phase is separated off, dried with magnesium sulphate and filtered. The filtrate is concentrated, the residue is digested with diethyl ether and the crystalline product is isolated by filtration under suction.

1.8 g (51%6+1 of theory) of 4-ethoxy-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 99° C. are obtained.

By the methods of Example (II-1) and/or by other known methods (cf. the publications mentioned above), it is also possible to prepare, for example, the compounds of the formula (II) below:

4-methyl-, 4,5-dimethyl-, 4-methyl-5-ethyl-, 4-methyl-5-n-propyl-, 4-methyl-5-i-propyl-, 4-methyl-5-n-butyl-, 4-methyl-5-phenoxy-, 4-methyl-5-methylthio-, 4-methyl-5-ethylthio-, 4-methyl-5-n-propylthio-, 4-methyl-5-i-propylthio-, 4-methyl-5-allylthio-, 4-methyl-5-propargylthio-, 4-methyl-5-cyclopropyl-, 4-methyl-5-chloro-, 4-methyl-5-bromo-, 4-methyl-5-methoxy-, 4-methyl-5-ethoxy-, 4-methyl-5-n-propoxy-, 4-methyl-5-i-propoxy-, 4-methyl-5-n-butoxy-, 4-methyl-5-cyclopropylmethoxy-, 4-methyl-5-cyclopropylthio-, 4-methyl-5-trifluoroethoxy-,4-methyl-5-dimethylamino-and 4-methyl-5-methylamino- -2,4-dihydro-3H- 1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-ethyl-, 4,5-diethyl-, 4-ethyl-5-methyl-, 4-ethyl-5-n-propyl-, 4-ethyl-5-i-propyl-, 4-ethyl-5-n-butyl-, 4-ethyl-5-phenoxy-, 4-ethyl-5-methylthio-, 4-ethyl-5-ethylthio-, 4-ethyl-5-n-propylthio-, 4-ethyl-5-i-propylthio-, 4-ethyl-5-allylthio-, 4-ethyl-5-propargylthio-, 4-ethyl-5-cyclopropyl-, 4-ethyl-5-chloro-, 4-ethyl-5-bromo-, 4-ethyl-5-methoxy-, 4-ethyl-5-ethoxy-, 4-ethyl-5-n-propoxy-, 4-ethyl-5-i-propoxy-, 4-ethyl-5-n-butoxy-, 4-ethyl-5-cyclopropylmethoxy-, 4-ethyl-5-cyclopropylthio-, 4-ethyl-5-trifluoroethoxy-,4-ethyl-5-dimethylamino-and 4-ethyl-5-methylamino-2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;

4-cyclopropyl-5-methyl-, 4-cyclopropyl-5-ethyl-, 4-cyclopropyl-5-n-propyl-, 4-cyclopropyl-5-i-propyl-, 4-cyclopropyl-5-n-butyl-, 4-cyclopropyl-5-phenoxy-, 4-cyclopropyl-5-methylthio-, 4-cyclopropyl-5-ethylthio-, 4-cyclopropyl-5-n-propylthio-, 4-cyclopropyl-5-i-propylthio-,4-cyclopropyl-5-allylthio-,4-cyclopropyl-5-propargylthio-, 4-cyclopropyl-5-cyclopropyl-, 4-cyclopropyl-5-chloro-, 4-cyclopropyl-5-bromo-, 4-cyclopropyl-5-methoxy-, 4-cyclopropyl-5-ethoxy-, 4-cyclopropyl-5-n-propoxy-, 4-cyclopropyl-5-i-propoxy-, 4-cyclopropyl-5-n-butoxy-, 4-cyclopropyl-5-cyclopropylmethoxy-, 4-cyclopropyl-5-cyclopropylthio-, 4-cyclopropyl-5-trifluoroethoxy-, 4-cyclopropyl-5-dimethylamino- and 4-cyclopropyl-5-methylamino-2,4-dihydro-3H- 1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-methoxy-, 4,5-dimethoxy-, 4-methoxy-5-methyl-, 4-methoxy-5-ethyl-, 4-methoxy-5-n-propyl-, 4-methoxy-5-i-propyl-, 4-methoxy-5-n-butyl-, 4-methoxy-5-phenoxy-, 4-methoxy-5-methylthio-, 4-methoxy-5-ethylthio-, 4-methoxy-5-n-propylthio-, 4-methoxy-5-i-propylthio-, 4-methoxy-5-allylthio-, 4-methoxy-5-propargylthio-, 4-methoxy-5-cyclopropyl-, 4-methoxy-5-chloro-, 4-methoxy-5-bromo-, 4-methoxy-5-ethoxy-, 4-methoxy-5-n-propoxy-, 4-methoxy-5-i-propoxy-, 4-methoxy-5-n-butoxy-, 4-methoxy-5-cyclopropylmethoxy-, 4-methoxy-5-cyclopropylthio-, 4-methoxy-5-trifluoroethoxy-, 4-methoxy-5-dimethylamino- and 4-methoxy-5-methylamino-2,4-dihydro-3H- 1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-ethoxy-, 4,5-diethoxy-, 4-ethoxy-5-methyl-, 4-ethoxy-5-ethyl-, 4-ethoxy-5-n-propyl-, 4-ethoxy-5-i-propyl-, 4-ethoxy-5-n-butyl-, 4-ethoxy-5-phenoxy-, 4-ethoxy-5-methylthio-, 4-ethoxy-5-ethylthio-, 4-ethoxy-5-n-propylthio-, 4-ethoxy-5-i-propylthio-, 4-ethoxy-5-allylthio-, 4-ethoxy-5-propargylthio-, 4-ethoxy-5-cyclopropyl-, 4-ethoxy-5-chloro-, 4-ethoxy-5-bromo-, 4-ethoxy-5-methoxy-, 4-ethoxy-5-n-propoxy-, 4-ethoxy-5-i-propoxy-, 4-ethoxy-5-n-butoxy-, 4-ethoxy-5-cyclopropylmethoxy-, 4-ethoxy-5-cyclopropylthio-, 4-ethoxy-5-trifluoroethoxy-, 4-ethoxy-5-dimethylamino- and 4-ethoxy-5-methylamino- -2,4-dihydro-3H- 1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-amino-, 4-amino-5-methyl-, 4-amino-5-ethyl-, 4-amino-5-n-propyl-, 4-amino-5-i-propyl-, 4-amino-5-n-butyl-, 4-amino-5-phenoxy-, 4-amino-5-methylthio-, 4-amino-5-ethylthio-, 4-amino-5-n-propylthio-, 4-amino-5-i-propylthio-, 4-amino-5-allylthio-, 4-amino-5-propargylthio-, 4-amino-5-cyclopropyl-, 4-amino-5-chloro-, 4-amino-5-bromo-, 4-amino-5-methoxy-, 4-amino-5-ethoxy-, 4-amino-5-n-propoxy-, 4-amino-5-i-propoxy-, 4-amino-5-n-butoxy-, 4-amino-5-cyclopropylmethoxy-, 4-amino-5-cyclopropylthio-, 4-amino-5-trifluoroethoxy-, 4-amino-5-dimethylamino- and 4-amino-5-methylamino-2,4-dihydro-3H- 1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-methylamino-,4-methylamino-5-methyl-,4-methylamino-5-ethyl-,4-methylamino-5-n-propyl-, 4-methylamino-5-i-propyl-, 4-methylamino-5-n-butyl-, 4-methylamino-5-phenoxy-, 4-methylamino-5-methylthio-, 4-methylamino-5-ethylthio-, 4-methylamino-5-n-propylthio-, 4-methylamino-5-i-propylthio-, 4-methylamino-5-allylthio-, 4-methylamino-5-propargylthio-, 4-methylamino-5-cyclopropyl-, 4-methylamino-5-chloro-, 4-methylamino-5-bromo-, 4-methylamino-5-methoxy-, 4-methylamino-5-ethoxy-, 4-methylamino-5-n-propoxy-,4-methylamino-5-i-propoxy-,4-methylamino-5-n-butoxy-, 4-methylamino-5-cyclopropylmethoxy-, 4-methylamino-5-cyclopropylthio-, 4-methylamino-5-trifluoroethoxy-, 4-methylamino-5-dimethylamino- and 4-methylamino-5-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H- 1,2,4-triazole-3-thione;

4-dimethylamino-, 4-dimethylamino-5-methyl-, 4-dimethylamino-5-ethyl-, 4-dimethylamino-5-n-propyl-,4-dimethylamino-5-i-propyl-,4-dimethylamino-5-n-butyl-, 4-dimethylamino-5-phenoxy-, 4-dimethylamino-5-methylthio-, 4-dimethylamino-5-ethylthio-, 4-dimethylamino-5-n-propylthio-, 4-dimethylamino-5-i-propylthio-, 4-dimethylamino-5-allylthio-, 4-dimethylamino-5-propargylthio-, 4-dimethylamino-5-cyclopropyl-, 4-dimethylamino-5-chloro-,4-dimethylamino-5-bromo-,4-dimethylamino-5-methoxy-, 4-dimethylamino-5-ethoxy-, 4-dimethylamino-5-n-propoxy-, 4-dimethylamino-S-i-propoxy-, 4-dimethylamino-5-n-butoxy-, 4-dimethylamino-5-cyclopropylmethoxy-, 4-dimethylamino-5-cyclopropylthio-, 4-dimethylamino-5-trifluoroethoxy-, 4-dimethylamino-5-dimethylamino- and 4-dimethylamino-5-methylamino-2,4-dihydro-3H- 1,2,4-triazol-3-one and 2,4-dihydro-3H- 1,2,4-triazole-3-thione.

Starting materials of the formula (IV):

Example (IV-1) ##STR223##

At 20° C., a solution of 15.0 g (103 mmol) of 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one in 120 ml of methylene chloride is admixed with a solution of 4.6 g of sodium hydroxide and 0.5 g of tetrabutylammonium bromide in 120 ml of water. A solution of 19.6 g (114 mmol) of O-phenyl chlorothioformate in 100 ml of methylene chloride is then added dropwise to this mixture at 20° C., and the reaction mixture is stirred at 20° C. for a further 12 hours. The crystalline product is isolated by filtration under suction.

25.6 g (88% of theory) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 242° C. are obtained.

Example (IV-2) ##STR224##

At 20° C., a solution of 29.6 g (206 mmol) of 4-methyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one in 240 ml of methylene chloride is admixed with a solution of 9.2 g of sodium hydroxide and 1 g of tetrabutylammonium bromide in 240 ml of water. A solution of 39.2 g (228 mmol) of O-phenyl chlorothioformate in 200 ml of methylene chloride is then added dropwise to this mixture at 20° C., and the reaction mixture is stirred at 20° C. for a further 12 hours. The organic phase is then separated off and the aqueous phase is extracted once more with 100 ml of methylene chloride. The combined organic phases are washed with 200 ml of water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is stirred with diethyl ether and the crystalline product is isolated by filtration under suction.

44.3 g (77% of theory) of 4-methyl-5-ethoxy-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 123° C. are obtained.

By the methods of Examples (IV-1) and (IV-2), it is also possible to prepare, for example, the compounds of the formula (IV) listed in Table 2 below. ##STR225##

                  TABLE 2                                                          ______________________________________                                         Examples of the compounds of the formula (IV)                                                                              Melt-                                                                          ing                                Ex.                                         point                              No.  Q.sup.1                                                                              Q.sup.2                                                                              R.sup.1      R.sup.2 Z     (° C.)                      ______________________________________                                         IV-3 O     S     CH.sub.3     C.sub.2 H.sub.5                                                                        OC.sub.6 H.sub.5                                                                     136                                IV-4 O     S     NH.sub.2     CH.sub.3                                                                               OC.sub.6 H.sub.5                                                                     177                                IV-5 O     S     NH.sub.2     N(CH.sub.3).sub.2                                                                      OC.sub.6 H.sub.5                                                                     161                                IV-6 O     S                                                                                    1            N(CH.sub.3).sub.2                                                                      OC.sub.6 H.sub.5                                                                     92                                 IV-7 O     S     NH.sub.2     OCH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     158                                IV-8 O     S     CH.sub.3     OC.sub.3 H.sub.7 -n                                                                    OC.sub.6 H.sub.5                                                                     90                                 IV-9 O     S     CH.sub.3     OCH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     186                                IV-10                                                                               O     S                  --(CH.sub.2).sub.5 --                                                                  OC.sub.6 H.sub.5                                                                     153                                IV-11                                                                               O     S                                                                                    2 #STR226##  OC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                                                                     148                                IV-12                                                                               O     S     CH.sub.3     CH.sub.3                                                                               OC.sub.6 H.sub.5                                                                     139                                IV-13                                                                               O     S     OC.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                                                                     98                                 IV-14                                                                               O     S     OCH.sub.3    SCH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     180                                IV-15                                                                               O     S     OCH.sub.3    SC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                                                                     100                                IV-16                                                                               O     S     N(CH.sub.3).sub.2                                                                           C.sub.3 H.sub.7 -n                                                                     OC.sub.6 H.sub.5                                                                     58                                 IV-17                                                                               O     S                                                                                    2 #STR227##  OC.sub.3 H.sub.7 -i                                                                    OC.sub.6 H.sub.5                                                                     89                                 IV-18                                                                               O     S                                                                                    2 #STR228##  N(CH.sub.3).sub.2                                                                      OC.sub.6 H.sub.5                                                                     154                                IV-19                                                                               O     S                                                                                    2 #STR229##                                                                                 2 #STR230##                                                                            OC.sub.6 H.sub.5                                                                     144                                IV-20                                                                               O     S                                                                                    2 #STR231##  S-C.sub.2 H.sub.5                                                                      OC.sub.6 H.sub.5                                                                     124                                IV-21                                                                               O     S     CH.sub.3     OC.sub.3 H.sub.7 -i                                                                    OC.sub.6 H.sub.5                                                                     108                                IV-22                                                                               O     S     C.sub.2 H.sub.5                                                                             OCH.sub.3                                                                              OC.sub.6 H.sub.5                                                                     122                                IV-23                                                                               O     S     OC.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                        OC.sub.6 H.sub.5                                                                     95                                 IV-24                                                                               O     S     CH.sub.3     Br      OC.sub.6 H.sub.5                                                                     211                                IV-25                                                                               O     S     CH.sub.3     OCH.sub.2 CF.sub.3                                                                     OC.sub.6 H.sub.5                                                                     122                                IV-26                                                                               O     S     OCH.sub.3    C.sub.3 H.sub.7 -n                                                                     OC.sub.6 H.sub.5                                                                     oil                                IV-27                                                                               O     S                                                                                    2 #STR232##  Br      OC.sub.6 H.sub.5                                                                     172                                IV-28                                                                               O     S                                                                                    2 #STR233##  CH.sub.2 OCH.sub.3                                                                     OC.sub.6 H.sub.5                                                                     74                                 IV-29                                                                               O     S     C.sub.2 H.sub.5                                                                             OC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                                                                     89                                 IV-30                                                                               O     S     CH.sub.3     SO.sub.2 CH.sub.3                                                                      OC.sub.6 H.sub.5                                                                     196                                IV-31                                                                               O     S     CH.sub.3     C.sub.3 H.sub.7 -n                                                                     OC.sub.6 H.sub.5                                                                     67                                 IV-32                                                                               O     S     CH.sub.3     C.sub.3 H.sub.7 -i                                                                     OC.sub.6 H.sub.5                                                                     96                                 IV-33                                                                               O     S     CH.sub.3     CH.sub.2 OCH.sub.3                                                                     OC.sub.6 H.sub.5                                                                     98                                 IV-34                                                                               O     S     CH.sub.3     SC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                                                                     130                                IV-35                                                                               O     S     CH.sub.2 --CH═CH.sub.2                                                                  OC.sub.2 H.sub.5                                                                       OC.sub.6 H.sub.5                         IV-36                                                                               S     O     CH.sub.3     H       OC.sub.6 H.sub.5                                                                     172                                ______________________________________                                    

USE EXAMPLES Example A Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered with the preparation of the active compound. It is advantageous to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds according to Preparation Examples 3, 23, 27 and 28, for example, exhibit a very strong action against weeds, while some of them are very well tolerated by crops, such as cotton.

                                      TABLE A                                      __________________________________________________________________________     Pre-emergence test/greenhouse                                                                       Appli-                                                                         cation                                                                         rate    Echino     Portu-                                                                             Sola-                              Active compound      (g/ha)                                                                             Cotton                                                                             chloa                                                                              Poa                                                                               Setaria                                                                            laca                                                                               num                                __________________________________________________________________________     3 #STR234##          60  0   95  95 90  95  95                                 4 #STR235##          60  0   80  95 90  70  90                                 5 #STR236##          60  0   95  95 95  90  90                                 6 #STR237##          60  0   95  95 95  95  95                                 __________________________________________________________________________

Example B Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are employed in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, the compounds of Preparation Examples 3, 15 and 28, for example, exhibit a very strong action against weeds, while being well tolerated by crops, such as wheat.

                                      TABLE B                                      __________________________________________________________________________     Post-emergence test/greenhouse                                                                      Appli-                                                                         cation                                                                         rate    Amaran-                                                                             Helia                                                                             Sola-                                     Active compound      (g/ha)                                                                             Wheat                                                                              thus nthus                                                                             num Xanthium                              __________________________________________________________________________     7 #STR238##          60  5   95   100                                                                               90  95                                    8 #STR239##          60  0   85   95 85  70                                    9 #STR240##          60  10  95   100                                                                               99  90                                    __________________________________________________________________________ 

What is claimed is:
 1. A sulphonylamino(thio)carbonyl-triazolin(ethi)one compound of the general formula (I) ##STR241## in which Q¹ represents oxygen,Q² represents sulphur, R¹ represents C₁ -C₆ -alkyl, or represents C₂ -C₆ -alkenyl, or represents C₃ -C₆ -cycloalkyl, R² represents C₁ -C₄ -alkoxy-substituted C₁ -C₆ -alkyl, or represents optionally fluorine substituted C₁ -C₆ -alkoxy, or represents C₁ -C₆ -alkylthio, or represents di-(C₁ -C₄ -alkyl)-amino, C₃ -C₆ -cycloalkyl, R³ represents the grouping ##STR242## in which R⁴ is identical or different and each represenst hydrogen, fluorine, chlorine, bromine, C₁ -C₆ -alkyl (which is optionally substituted by fluorine), or represents C₂ -C₆ -alkinyl (which is optionally substituted by fluorine), or represents C₁ -C₄ -alkoxy (which is optionally substituted by fluorine), C₁ -C₄ -alkylthio or represents the radical --S(O)_(p) --R⁶ in whichp represents the number 2 and R⁶ represents C₁ -C₄ -alkyl, di-(C₁ -C₄ -alkyl)-amino R⁴ further represents phenyl R⁵ represents hydrogenand the sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, tetra-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-sulphonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salt thereof.
 2. Compounds of the formula (I) according to claim 1, whereinQ¹ represents oxygen, Q² represents sulphur, R¹ represents optionally ethoxy-substituted methyl, ethyl, propenyl, cyclopropyl, R² represents hydrogen, or represents optionally methoxy-substituted methyl, ethyl, n or i propyl, or represents respectively optionally fluorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, or represents dimethylamino, or represents cyclopropyl, R³ represents the radical ##STR243## in which R⁴ represents fluorine, chlorine or bromine, or represents optionally fluorine-substituted methyl, or represents optionally fluorine-substituted methoxy, methylthio, methylsulphonyl, ethylsulphonyl, dimethylaminosulfonyl, phenyl, andR⁵ represents hydrogen.
 3. An herbicidal composition which comprises an herbicidally effective amount of a compound according to claim 1 and an inert carrier.
 4. A method of combatting unwanted plant growth which comprises applying to said unwanted plant or to an environment in which it is desired to exclude said unwanted plant an herbidically effective amount of a compound according to claim
 1. 